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Overnight Success: The Long Game

Benjamin Disraeli, former British Prime Minister, once said “the secret of success is for a man to be ready for his opportunity when it comes.” Disraeli’s quote focuses on the prep time spent in the shadows for that moment in the spotlight.  Collins Dictionary defines ‘overnight success’ as something that becomes successful very quickly.  Most of us desire to be an overnight success but sometimes it takes years to become one. 

Bernardine Evaristo in her book, Manifesto, said  “I wasn’t an overnight success, but everything changed overnight.”  She would unpack this further in the book with  “When I won the Booker Prize in 2019 for my novel Girl, Woman, Other, I became an ‘overnight success’ – after forty years working professionally in the arts. My career hadn’t been without its achievements and recognition, but I wasn’t widely known. The novel became a #1 bestseller sold in many foreign languages and received the kind of attention I had long desired for my work.”

Jose Mourinho, a football manager, at the peak of his managerial powers in 2004 said that “after 15 years, I’m an overnight success.” 

To become an overnight success requires stamina and perseverance because there would be certain periods when giving up seems a better option than going on. This requires the willingness to play the long game even if there are no guarantees of becoming an overnight success. 

The true motivation for creative work shouldn’t be the spotlight but for the production of the creative outputs. You have no control over how the world reacts to your creative outputs. You only have control over the production of your outputs. Hence you keep on creating because you don’t know which piece of work would resonate with a huge audience. Every piece of new work builds on the previous one and this helps you improve your craft and your creative voice. 

I can guarantee that if Bernardine Evaristo’s novel wasn’t a runaway hit; she would still keep writing books and doing the work. Winning the 2019 Booker prize and getting international recognition is a wonderful bonus. There is no guarantee that her next book will get similar accolades but that won’t stop her because she is playing the long game.

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Determining the Right Time

Perfect Moment & Right Time

So often we find we are stuck in that place of waiting for the “perfect moment” even though experience shows us that there really isn’t such a thing.
Yet still, there is also the challenge of striking too early.
I’d be interested to read your thoughts on some pragmatic steps to determine the right time to engage.

A friend of mine posted the above comment in LinkedIN in response to my last blog post.

I find that the concept of the “right time” to be a subset of the “perfect condition or moment.” It is very easy to get paralysed waiting for the “right time” or the “perfect moment”.

My good friend asked me for pragmatic steps. Here are my thoughts:

(1) Know thyself
The philosophical question is what is the definition of the “right time”? The response to this question differs for each individual. My right time is different from your right time despite both of us pursuing similar goals and desiring similar outcomes. The decision when to start a thing is dependent on internal factors, external factors or a mixture of both. There is little benefit pursuing your dreams in competition with other people because there are just too many variables in play. This is also a recipe for an anxious life when your expectations don’t align with reality in comparison to others. Focus on your own race and be happy for others when they succeed in their own.

(2) Risk taking appetite
The right time is also dependent on your appetite for risk taking. Some people are willing to abandon a well paying but unfulfilling job to pursue the dream of becoming an entrepreneur without a safety net. Others want their affairs in order before jumping out in pursuit of their dreams. The right time” threshold for a risk averse person is higher than that of a risk tolerant person.

(3) Strategic payoff
The right time for a project will also hinge on the timing of the payoff. It would be sensible to start a long term project as soon as possible e.g. the best time to plant an oak tree is 30 years ago and the second best time is today. This same principle applies to your financial investments for retirement depending on your age.

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Perfection & Procrastination

“If you wait for perfect conditions, you will never get anything done.” Ecclesiastes 11:4 {New Living Translation}

I am always waiting for the perfect conditions to pursue my creative projects. I am the great procrastinator. I want my inspiration before perspiration. My inspiration operates on an elephant’s pregnancy time frame birthing procrastination.

There is also the creative block of sharing any work with the public because of an unrealistic desire for perfection.

The first rule of writing is to write. That’s the only thing I have control over; the public’s response or lack of it is outside my control. I have to be happy with my output and let go of the outcome.

It’s time to stop waiting for perfect conditions and instead work within the realms of constraints. Creativity is birthed from the wombs of constraints not from the tombs of perfect conditions

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Knee Pads vs Packing Tables.

This interesting anecdote about Amazon is sourced from the book – The Bezos Letters. Two men experiencing the same pain point but had two different solutions to it. 

The pain point was a result of constant kneeling and the natural instinct was to get rid of this pain. Jeff Bezos, Amazon’s CEO, went with the straightforward solution – get knee pads. Yes, this would solve his knee pain but it was also a tactical solution rather than a strategic one.

The real user need in this scenario was the ability to pack the boxes in the most comfortable and efficient way. This is what makes the packing table idea a better solution compared to the knee pads option. 

Jeff Bezos quickly realised that packing tables was a better strategic solution for the packers and dropped his own idea in favour of it.

I work as a user researcher and my job is to talk to users to unpack their needs and pain points. I then work with the product team to come up with product solutions to address these user needs and pain points. It is very easy to gravitate towards “knee pad” product solutions which meet the tactical needs of some users. The challenge is to come up with strategic “packing table” product solutions for the majority of users. 

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The Journaling Habit

On 10 July 2013, I got the Day One app for free from Apple. This was a result of the company celebrating the fifth anniversary of its app store. Day One is a daily journaling app which I used rarely until 2015 when I used it a lot that year. I went back to using it rarely until 1 January 2020 when I kickstarted a journaling habit. Since then until today, I haven’t missed a day. My streak is 455 days uninterrupted. I have wondered why the journaling habit clicked in 2020 but not in any of the preceding seven years.

Three things have helped me maintain my daily journaling streak.


(1) I built journaling into my daily routine.

Before the first Covid lockdown in the UK in March 2020; I would journal during my morning commute on the train. Since I started working from home; I have shifted my journaling to the evenings before going to bed. It is a chance to reflect on the highlights of the day and capture my thoughts. A journal is a great place to take the time to converse with yourself.


(2) No word count targets.

I used have a writing word target of 500 words per daily journal entry. I found this to be a strait jacket because it sucked the fun out of journaling. I was trying to hit this target even when I didn’t have much to say that day. Now, I write as much or as little as I like. The goal of journaling is to write something authentic about my daily experience. This could be one word or a million words.


(3) Day One’s “On this day” feature.

I never engaged with this feature until recently and it has been a game changer. There are currently 693 Day One journal entries over the past 8 years. I would like to re-read all these entries for recurring themes but this is an overwhelming task. The “on this day” feature helps me tackle this. Day One gives me the ability to read all the previous entries {if any} I have written each day over the past seven years. This allows my present self to interact with my past self.


I have found journaling to be a great reflective practice and would recommend the habit. Day One is a great app for this if you are looking for a journaling app.

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An Obit A Day

I started 2021 with a series of daily habits to do. Several of them flamed out by mid-January. One of the ones going strong is reading an obit a day. I was inspired by Austin Kleon who in his Show your Work book recommended the practice of reading obituaries daily.

I tried to get into the habit a few years ago but it never lasted. The reason was because I didn’t have a process to help me make the activity fun and keep me motivated. It is easy to get overwhelmed by sheer amount of daily obituaries. 

I have one rule to tackle this; only select the daily obit from one of two sources: The Guardian (UK) or New York Times (US). Both give me a good coverage of notable and notorious deaths. I follow the obituary departments’ Twitter accounts for both papers: @guardianobits and @NYTObits. Every evening I scroll through them and identify one obit to read for that day. After reading the obit, I will select the most interesting quote and share it on Twitter with a link to the source material. This directs folks who come across my obit tweet to the obituary if they like the quote about the person. 

Here are some of my personal favourite obit tweets so far:

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Following my Curiosities

Image source: Eflon

It is 2021 and I want to get back into the habit of blogging. I used to blog regularly several years ago and lost momentum. I am a natural procrastinator and if given the opportunity I would procrastinate. My target for 2021 is to write at least 2 blog posts per month and I am making this public so I can hold myself accountable.

What will I blog about?

This has been my biggest mental block and reason for not writing much in the last few years. I couldn’t determine what I wanted this website to be about. Did I want to talk about work related topics or personal interest topics? I was stuck and that led to little creative output. I was also trying to write content that other people would like to read instead of topics that interested me. I realised that I had to be true to myself. The first step towards change is self-awareness.

I am going to follow my curiosities via my blog and see where they lead in in 2021. I invite you to join me on this trip. I have a good feeling that we would learn some interesting things along the way.

Happy New Year.

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UCB Word for Today Sample Dialog

Conversation design is about teaching computers to be fluent in human conversation and its conventions.” {Source}

I recently got interested in conversational design and started learning more about the topic via Medium articles, YouTube videos and podcasts. I will curate a list of some of the most useful resources in a future post.

“The role of a conversation designer is like that of an architect, mapping out what users can do in a space, while considering both the user’s needs and the technological constraints. They curate the conversation, defining the flow and its underlying logic in a detailed design specification that represents the complete user experience. They partner with stakeholders and developers to iterate on the designs and bring the experience to life.” {Source}.

A sample dialog is a key tool for conversational designers to map out the interaction between the users and a voice bot. It outlines the conversation flow between a user and a voice bot as they take turns. Sample dialogs are like movie scripts.

Conversational designers create sample dialogs before developers starting coding because they help highlight potential issues so that valuable time and effort aren’t wasted creating the wrong voice product. 

I am a big fan of the UCB Word for Today devotional. which I read every day on my mobile device. I discovered that there is currently not an Alexa Skill/Google Action for it but this is a product that could work as a Skill/Action. I don’t have the skills to build a Skill or Action yet so I focused on developing a happy path sample dialog for a UCB user (below).

I first mapped a sample dialog on the wall using Post it Notes. This gave me the flexibility to move around things, bin notes that didn’t work so I could create a happy path.

First draft

I looked for a free sample dialog builder online but couldn’t find anything satisfactory so I ended up using Google Sheet which met my needs.

Polished draft
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Context Interpreters

Image by @olaojo15

I watched a Creative Mornings talk by Alan Webber today. Webber was the co-creator of one of my favourite business magazines – Fast Company. His talk was on the importance of context over content. He argues that context not content is king in a world battling information overload. People need help to make sense of the content they are consuming.

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UX Design Challenge Submission

I attended the UX in the City conference a few days ago and really enjoyed it. I took part in a UX design challenge posed by one of the conference’s sponsors – ECOM Recruitment. It was a chance for me to apply my UX skills.

The challenge called “Careers Page Conundrum” required participants to redesign a careers’ page in order to meet the needs of two personas.  There were prizes for the best three submissions.

This blog post is a quick documentation of my thought process behind my submission.